Samantha Tracey’s Pissed Connections – Dating an Older Woman

Dear Pissed Connections,

I’m a 22-year-old dude who moved to Boston a few months ago for work. I’ve got stellar job, a first-rate circle of friends and a great apartment. My only problem is, I’m having a hard time meeting “that special someone.”

There is this woman in my circle of friends I’m crushing on badly – the tricky part is, she’s 37. Now, I have no problem pursuing an older woman, but I can tell she’s not into me strictly because I’m so much younger.

How can I get to see her to see me beyond my age?! I want to show her just how much man she’s missing out on.


Cougar Hunter

Dear Cougar Hunter,

You’ve got your work cut out for you. Hunting a cougar is like….

Well, hunting a cougar. They’re sharp, fast and vicious.

Just ask their ex-husbands.

What you need to do is mold yourself into the older man she’s yearning for. Change your personality and wardrobe completely.  Remember: You want a woman to love you for the man you’re pretending to be, not the man you are.

Step 1. Transform.

Every woman wants to be dating George Clooney. So, become him. Dye your hair to achieve the “salt and pepper” look. (Avoid the “silver fox”— this is for my intermediate students). Maintain a 5 o’clock shadow at all times. Wear a watch. Carry a briefcase. Use a shoehorn.

Step 2. Talk the talk.

To prove you have mature values, talk about subjects old people talk about. Retirement plans, booming college tuitions, arthritis and high cholesterol are all acceptable.

Step 3. Engage with the cougar.

Once you’ve proven your maturity by declaring your appreciation for prunes and their benefits, ask her about herself. But keep the topics mature. Ask her how she feels about her laugh lines, her crowfeet and her ticking biological clock. She’ll be flattered you’re so in-tune with the anxieties of a woman in her thirties.

Step 4. Drop the bait.

Now that you’ve got her attention, win her over. Let her know you’re more than your age by… acting more than your age. Typical 20-somethings will buy a girl a drink or 4, hoping to impress her while boozing her up.

Show this cougar you’re not so predictable. Does a real man buy a woman drinks? No. Does a real man hold a door for a woman? Nah. Does a real man ask her for her number? Hell, no! He asks her to connect on LinkedIn.

So. Damn. Professional.

Once she’s accepted your request, she may as well be accepting your marriage proposal – this woman’s so into you. Just keep up the façade (forever) and you’ll grow old and gray together. Well, she’ll grow older and grayer.

Happy hunting,

Pissed Connections

Can’t tell if your girlfriend is on her period or if she’s just a full-time bitch? I’ve got you covered. For advice on dating, mating and ex-boyfriend berating, send an e-mail to [email protected].